Potassium Carbonate → HCID 11256916, compound

HRID 722249Notes

Reaction equation

[Cl:1][C:2]1[C:3]2[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][NH:9][C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1.Cl[CH2:16][C:17]1[C:22]([CH3:23])=[C:21]([O:24][CH3:25])[C:20]([CH3:26])=[CH:19][N:18]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[C:3]2[C:11]([CH:12]([CH3:14])[CH3:13])=[CH:10][N:9]([CH2:16][C:17]3[C:22]([CH3:23])=[C:21]([O:24][CH3:25])[C:20]([CH3:26])=[CH:19][N:18]=3)[C:4]=2[N:5]=[C:6]([NH2:8])[N:7]=1

Participants

Conditions

Temperature: 45 °C

Procedure

A suspension of 4-chloro-5-isopropyl-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine (105 mg, 0.5 mmol), 2-chloromethyl-4-methoxy-3,5-dimethyl-pyridine (93 mg, 0.5 mmol) and K2CO3 (85 mg, 0.6 mmol) in dry DMF (1 mL) was heated to 45° C. overnight, Work-up (EtOAc), evaporation, and purification by preparative TLC (MeOH/CH2Cl2 10:1) gave 4-chloro-5-isopropyl-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamine (36 mg). HPLC Rt: 5.867 min. 1H-NMR (DMSO-d6): δ 8.07 (s, 1H), 6.74(s, 1H), 6.51 (s, 2H), 5.22 (s, 2H), 3.70 0s, 3H), 3.23 (7, 1H), 2.21 (s, 3H), 2.15 (s, 3H).

Workup

custom(EtOAc), evaporation, and purification by preparative TLC (MeOH/CH2Cl2 10:1)

Sources & evidence

ORD record: ord-127ed21a7d1b4180915ca94c07832979
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07138402B2

Reaction notes

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